• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The invention relates to substituted hemidazopyrimidines, in particular, the general formula Ra-XG lSf-C i I H2-C Crg H-CH C-C -C 5, n-alkenyl-Cz-Cg, dicloalkyl-C-C. - lower alkyl, benzyl, or R2-alkylene-Cd-Su, EZ-lower alkyl, or their addition salts with acids, which have pharmacological properties and can be used in medidin. For the detection of activity in substituted imidazopyrimidines, new ones were obtained 1. Their synthesis is carried out from the corresponding quinazolinamine from halophenylprop The -1,2-dione in a solvent medium followed by the dicycadium of the product obtained in a solvent medium at the boiling point. Isolation 1 is carried out either as a base or as an additive salt after treatment with an appropriate acid. Tests 1 show that they show biochemical activity of benzodiazepines to the receptors, suppressing by 50% the specific binding of fpunitrazepam to preparations of rat forebrain membranes. In addition, Compound 1 has a sedative effect on anxiety. 6 tab. with (Y) N9 00 vj SP IND S
    公开号:SU1287752A3
    申请号:SU833643057
    申请日:1983-08-26
    公开日:1987-01-30
    发明作者:Роже Тюлли Вильфред
    申请人:Руссель-Юклаф (Фирма)；
    IPC主号:
    专利说明:

    eleven
    This invention relates to a process for the preparation of new imidazo C1,2-a) pyrimidines or their salts.
    The purpose of the invention is the synthesis of new compounds possessing valuable pharmaceutical properties allowing their use in medicine.
    Example 1. 5-Ketoxy-6,7,8,9- -tetrahydroimidazoC1,2-a) quinazolin-2-yl / phenylmethanone.
    At room temperature, a solution of 20 g of 4-methoxy-5,6,7,8-tetrahydro-2-quinazolinam and 28.6 g of 3-bromo-1-phenylpropane-1,2-dione is stirred overnight. 400 cm of ethyl ether. The precipitated bromide, 4-methoxy-1- (3-phenyl -2,3-dioxopropyl) -5,6,7,8-tetrahydro-2-quinazolinimine, is filtered off, washed with ether, introduced into suspension in methanol and Heat for 2 hours with reverse cooling.
    The resulting solution was evaporated to dryness under reduced pressure, the residue was taken up in a mixture of chloroform and an aqueous solution of potassium carbonate. Washed the organic layer, dried
    it and evaporated to dry under reduced
    pressure.
    The residue is triturated in methanol, the crystals formed are filtered off and 18 g of the expected product are obtained. M.p. 234 C.
    Example 2-48. Similarly to Example 1, but based on the corresponding compounds of Formula 11, where R, Rj, R, and X have the meanings indicated in Table 1, new products were prepared. The spectrometric analyzes, the yields and melting points of the compounds obtained are also given in Table 1. Microanalysis is given in table 2.
    Example 49. 6-Ethyl-5-methyl-7- (methylthio) imidazo (1, 2-cx) pyrimidine-2 yl) phenylmethanone.
    4.5 g of 5-ethyl-4-methyl-6- (methylthio) -2-pyrimidines per 28 cm of ethyl ether are introduced into suspension, and then 5.5 g of 3-bromo-1-fench1pro pan-1 are added. , 2-dione.
    After 2 days at room temperature and with stirring, the resulting salt of pyrimidinium is filtered off and washed with ethanol under reflux. I evaporate pacTBCJip under reduced pressure and take the residues into the chloro-5 mixture
    77
    five

    50
    V)
    35

    -50
    55
    52 2 form and an aqueous solution of potassium carbonate.
    The organic layer is washed, dried and evaporated to dryness under reduced pressure, the residue is triturated in ethanol, the crystals are filtered off with suction, recrystallized in methanol and 4.1 g of the expected product are obtained.
    Examples 50-53. Analogously to example 49, but using as starting material the corresponding compounds of formula 1J, where R,, R, X are as indicated in Table 3, the compounds of Examples 50-53 were obtained. Spectrometric analyzes of the yields, and the melting points of these compounds are also given in Table 3. The results of microanalysis are given in table 4.
    EXAMPLE 50. 5-Ketil-7- (methyl-tis) -6-n-propylimidazoC 1, 2-C1) pyrimidin-2-yl / phenylmethanone.
    EXAMPLE 51 6-Allyl-5-methyl-7- - (methylthio) imidazo (1,2-a) pyrimidin--2-yl) phenylmethanone.
    Example 52. 5,6-Diethyl-7- - (methylthio) imidazo (1,2-a) pyrimidine-2-yl / phenylmethanone.
    Example 53. 5-Ethyl-7- (methylthio) -6-n-propylimidazo (1,2-a) pyrimidin-2-yl / phenylmethanone.
    Example 54. 6-Ethyl-7-methoxy-5-methylimidazo (1,2-a) pyrimidine-2-yl / -4-methoxyphenyl / methanone,
    6-ethyl-7-methoxy-5-methyl-1-imidazo (1,2-a) pyrimidine-2-carboxylic acid ethyl ester.
    At room temperature, a solution of 50.1 g of 5-ethyl-4-methoxy-6-methyl-2-pyrimidinamine and 70.2 g of bromopyruvic acid ethyl ester is stirred for 24 hours in 300 cm of ethyl ether, the precipitate is filtered off and washed ether and dried g. Put it in suspension in
    ethanol and then heated
    250 cm3
    2 hours with reflux. Cool, evaporate to dryness, and add to the residue a mixture of chloroform and 5% aqueous sodium bicarbonate solution. Decant, re-extract the aqueous layer with chloroform, combine the organic layers, dry them and evaporate the solvent.
    The expected product is obtained in the form of white crystals, which are purified by chromatography on silica, eluting with a mixture of chloroform and ethyl acetate (7-3). Obtain 31.4 g of product, which is triturated in a mixture of ethyl acetate - ether. Then it is filtered, dried and receive the target product with so pl.151- -.
    6-Ethyl-7-methoxy-5-methylimidazo (1,2-a) pyrimidin-2-yl / -methanol. Under stirring with fO, 11.55 g of lithium borohydride is added in small fractions over one hour to a solution of 19.7 g of the product obtained in 300 cm of anhydrous tetrahydrofuran. The mixture is stirred at room temperature for 18 hours; 5 excess of borohydride is destroyed by adding 300 cm of excess sodium chloride solution, stirred anew 30 minutes, and then decanted. The aqueous layer is extracted with chloroform, the organic layers are combined, dried and the solvent is evaporated. Get it. 15.4 g of the desired product with a melting point of 186-188 ° C. 6-Ethyl-7-methoxy-5-methyl imide water layer with chloroform, the organic layers are combined, dried and evaporated to dryness.
    The residue is chromatographed on silica, eluting with a mixture of h.por form-ethyl acetate (7-3), and 2.3 g of the expected product are obtained in the form of white crystals. M.p. 117-119 ° C.
    6-Ethyl-7-methoxy-5-methylimidazo (1,2-a) pyrimidin-2-yl (-) 4-meth-6-phenyl / methanone.
    10 g of activated manganese dioxide was added to a solution of 2.2 g of the product obtained in step g in 100 cm of chloroform, and then stirred for 18 hours at room temperature. Filter the mixture, evaporate the filtrate, purify the residue by chromatography on silica, eluting with chloroform-methanol (98-2), and obtain 1.3 g of the desired product. M.p. 196-197 ° C.
    Example 55-76. Similarly
    zo (1,2-a) pyrimidine-2-carboxaldehyde, 54, but was running out
    guide.
    40 g of activated manganese dioxide was added to a solution of 15.25 g of the product obtained in 200 cm of chloroform. The mixture is heated under reflux for 18 hours, 20 g of activated manganese dioxide are added, a. then continue heating under reflux for another 4 hours. Filter the cooled mixture, evaporate the filtrate and obtain 10.9 g of the desired product. M.p. 185-186 c.
    Calculated,%: C 60.0; H 6.0-, N 19.05,
    С „Н, ЗКз02
    Found,%: C 60.26; H 5.98 N 19.17.
    6-Ethyl-7-methoxy-5-methyl shd-30 (1,2-a) pyrimidin-2-yl) -4-methoxy-45 phenyl / methanol. .
    A 4-methoxyphenyl magnesium bromide solution is prepared by treating 0.54 g of magnesium shavings with
    4.20 g of para-bromoanisole in 25 cm without-50 -2-yl (2-pyridinyl) methanone. aqueous tetrahydrofuran. The resulting PRI me R 62. b-Ethyl-7-methoxy solution was added dropwise with a re-5-methylimidazo (1,2-a) pyrimidine-2-stirring to a solution of 1.64 g obtained -yl (4-fluorophenyl) methanone. In stage b of the product in 100 cm. EXAMPLE 63 b. Ethyl 7-methoxy-anhydrous tetrahydrofuran. Per-55 -5-methyl-imidazo (1,2-C1) pyrimidine is stirred at room temperature with 2-yl (3-trifluoromethyl) phenyl / methanone, for an hour, pour the mixture into Example 64. 1- / 6-Ethyl- 7-method octane aqueous solution of si-5-methylimidazo (1,2-ct) chloride ammonium pyrimidine, decanted, extracted with 2-yl / ethanone,
    the corresponding compounds of formula 11, wherein R, Rg, Rj, and X are as indicated in Table 5, the compounds of Examples 55-76 were obtained. 30 Example 55, 6-Ethyl-7-methoxy-5-methyl-imidazo (1,2-a) pyrimidine-2-yl-4-chlorophenyl / methanone.
    EXAMPLE 56. b-Ethyl-7-methoxy-5-methyl-imidazo (1,2-a) pyrimidine-2- 35 -yl-4-methylphenyl / methanone.
    PRI me R 57. b-Ztsh1-7-labels-. si-5-methylimidazo (1,2-a) pyrimidin- -2-yl -2-hpriphenyl / methanone.
    PRI me R 58. 6-Ethyl-7-methoxy-40 si-5-methylimidazo (1,2-a) pyridimidin-2-yl-3-methoxyphenyl / methanone.
    EXAMPLE 59 6-Ethyl-7-methoxy-5-methyl-imidazo (1,2-a) pyrimidin-2-yl-4-methylthiophenyl / methanone.
    Example 60.6- Ethyl-7-methoxy-5-methylimidazo (1,2-O.) pyrimidn--2-yl (2-thiensh1) methanone.
    EXAMPLE 61 1 6-Etsh1-7-netoksi-5-methylimidazo (1,2-a) pyrimidine-water layer with chloroform, the organic layers are combined, dried and evaporated to dryness.
    The residue is chromatographed on silica, eluting with a mixture of porous form ethyl acetate ester (7-3) and 2.3 g of the expected product are obtained in the form of white crystals. M.p. 117-119 ° C.
    6-Ethyl-7-methoxy-5-methylimidazo (1,2-a) pyrimidin-2-yl (-) 4-meth-6-phenyl / methanone.
    10 g of activated manganese dioxide was added to a solution of 2.2 g of the product obtained in step g in 100 cm of chloroform, and then stirred for 18 hours at room temperature. Filter the mixture, evaporate the filtrate, purify the residue chromatographically on silica, eluting with chloroform-methanol (98-2), and obtain 1.3 g of the desired product. M.p. 196-197 ° C.
    Example 55-76. Similarly
    Example 54, but consumed at the end
    five
    0 -2-yl (2-pyridinyl) methanone. Example 62. b-Ethyl-7-methoxy-5-methyl-imidazo (1,2-a) pyrimidine-2-yl (4-fluorophenyl) methanone. EXAMPLE 63 b-Ethyl-7-methoxy-5 -5-methyl-imidazo (1,2-C1) pyrimidin--2-yl (3-trifluoromethyl) phenyl / methanone, Example 64. 1- / 6 -Ethyl-7-methoct Si-5-methylimidazo (1,2-ct) pyrimidine- -2-yl / ethanone,
    the corresponding compounds of formula 11. Where R, Rg, Rj and X are as indicated in Table 5, the compounds of Examples 55-76 were obtained. 0 Example 55, 6-Ethyl-7-methoxy-5-methylimidazo (1,2-a) pyrimidine-2-yl-4-chlorophenyl / methanone.
    PRI me R 56. b-Ethyl-7-methoxy-5-methylimidazo (1,2-a) pyrimidine-2-5-yl-4-methylphenyl / methanone.
    PRI me R 57. b-Ztsh1-7-labels-. si-5-methylimidazo (1,2-a) pyrimidin- -2-yl -2-hpriphenyl / methanone.
    EXAMPLE 58. 6-Ethyl-7-methoxy-0 Cy-5-methyl-imidazo (1,2-a) pyridimidin-2-yl-3-methoxyphenyl / methanone.
    EXAMPLE 59 6-Ethyl-7-methoxy-5-methyl-imidazo (1,2-a) pyrimidin-2-yl-4-methylthiophenyl / methanone.
    Example 60.6- Ethyl-7-methoxy-5-methylimidazo (1,2-O.) pyrimidn--2-yl (2-thiensh1) methanone.
    EXAMPLE 61. 1 6-Etsh1-7-netoksi-5-methylimidazo (1,2-a) pyrimidine 512877526
    EXAMPLE 65 1-b-Ethn.n-7-Means The values given in Table 6 are effective minimum doses at which an increase in shocks with respect to controls (DEM mg / kg po ).
    15
    20
    toxi-5-metsh1IMidazo (1, 2-O-) pyrimidin-2-yl propanone,
    Example 66. 1-6-Ethyl-7-methoxy 5-methylimidazo (1,2-a) pyrimidine-5 -2-yl | butanone.
     R
    EXAMPLE 67 1-6-Ethyl-7-methoxy-5-methylimidazo (1,2-a) pyrimidin-2-yl-pentanone.
    PRI me R 68. b-Ethyl-7-methoxy-O
    -5-methylimidazo (1,2-O.) pyrimidine-2- -yl or cyclopropylmethanone.
    EXAMPLE 69, 6-Ethyl-7-methoxy 5-methylimidazo (1,2-c-Pyrimidine-2-yl cyclopentylmethanone.
    Example 70.b-Ethyl-7-methoxy-5-methylimndazo (1,2-a) pyrimidine-2-yl or cyclohexylmethanone.
    EXAMPLE 71. 1-6-Ethyl-7-metoxy-5-methylimidazo (1,2-cx) pyrimidin-2-yl, -4-penten-1-one.
    Example 72. 1-6-Ethyl-7-methoxy-5-methipimidazo (1,2-a) pyrimidine-2-yl -2-cyclohexyl-ethanone.
    Example 73. 6-Ztil-7-methoxy-5-methylimidazo (1,2-a) pyrimidine-2-yl -1-naphthylmeta non.
    Example 74. 6-Ethyl-7-methoxy-5-methyl-imidazo (1, 2-o.) Pyrimidin-2-yl (4-dimethyl inophenyl) methanone.
    Example 75. 1-6-Ethyl-7-methoxy-5-methylimidazo (1,2-a) pyrimidin-2-yl -2-methyl-2-propen-1-one.
    PRI me R 76. 1-: 6-Ethyl-7-methoxy-5-methyl-imidazo (1,2-O) pyrimidine-35 -2 yl-3-methyl butane.
    Spectrometric analyzes, yields, melting points and microanalysis of the compounds are also given in Table 5. Biochemical activity. The affinity of the compounds for benzodiazepine receptors was evaluated using the radioligan (3N) phpunitrase and the known method (modified).
    25
    thirty
    40
    45
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining imidazo (1,2-th) - pyrimidines of the general formula
    D v n j
    1l al.
    HtGhGSOR,
    B VJ- XX T T
    RI
    where X is sulfur, or oxygen; Rj - the same or different
    a hydrogen atom, a C – C alkyl straight linear radical, a C 2 –C straight linear radical, or an alkyl radical (cycloalkyl) C 1 –C lower alkyl, benzyl,
    or R and Rj are together the linear radical of Cj-C alkylene, R.J is lower alkyl,
    or their acid addition salts, characterized in that the compound of the general formula
    Yao-cht
    where X, R, R3 have the indicated meanings,
    subjected to interaction with the compound of the formula
    Y - CHj-CO - CO - Ph, // where Y is a halogen,
    The values shown in Table 6 are the nanomolecular concentrations of the test product, which suppress in a 50% ratio the specific bond of 0.6 nanomoles (ZN) of flunitrazepam of the membranes from the rat forebrain (SBU) in nanomoles.
    Pharmacological activity.
    A study of the sedative anxiety activity of the compound was carried out according to a known method (modified).
    Invention Formula
    The method of obtaining imidazo (1,2-th) - pyrimidines of the general formula
    D v n j
    1l al.
    HtGhGSOR,
    B VJ- XX T T
    RI
    where X is sulfur, or oxygen; Rj - the same or different
    a hydrogen atom, a C – C alkyl straight linear radical, a C 2 –C straight linear radical, or an alkyl radical (cycloalkyl) C 1 –C lower alkyl, benzyl,
    or R and Rj are together the linear radical of Cj-C alkylene, R.J is lower alkyl,
    or their acid addition salts, characterized in that the compound of the general formula
    Yao-cht
    where X, R, R3 have the indicated meanings,
    subjected to interaction with the compound of the formula
    Y - CHj-CO - CO - Ph, // where Y is a halogen,
    in the medium of a solvent, and the resulting compound of the general formula
    Ttj-x
    0
    Rjvs
    RI CH -CO-CO-Ph
    tl
    where Rj - Rj, y- have the indicated meanings, cyclization is performed while the reaction mass is boiled in a solvent medium and the desired product is isolated in the free form or as an acid salt of the acid.
    Priority by featured; 08.28.82 - at X - oxygen or sulfur, R, and Rj are the same or different, a hydrogen atom is molyl, a hydrogen atom is a C – C5 linear linear radical, a C – Cg alkenyl molar radical, and a (cycloalkyl) C radical -Cg-lower al-g
    the C-C-alkyl radical of the line, R - 5 t R and Rj are straight linear
    1shzshiy alkyl-,
    02.02.83 - with X - oxygen or sulfur, R and R are identical or decompose C, -C.-alkylene, lower alkyl.
    12877528
    individual, a hydrogen atom, a C – C5 linear linear radical, an alkyl radical, a C -Cg-alkenyl radical, a (cycloalkyl) C -Cg-lower al-g radical
    -5 t R and Rj - together linear
    t R and Rj - together linear
    radical With, -C.-alkylene, lower alkyl.
    Table 1
    table 2
    323.4
    14
    295.3
    15 b% Ks02
    281.3
    295, 3
    17CjgH N O
    321.4
    18CD.ZOZ
    337.4
    nineteen
    c, Ng / s (
    351.2
    20
    307.4
    21q5 "i, N30S
    283.4
    22qgH NjOS
    3J1H
    23.
    321.4
    Continued table. 2
    5, 30
    5.3
    5.80
    5.8
    5.37
    5.4
    5.80
    5.8
    5.96
    6.0
    5.68
    3.7
    7.17 7.1
    5.58
    5.6.
    4.62
    4.7
    12.999.91 (S)
    13,010,0
    14.23 1.3
    14.94 15.0
    14.23 14.2
    13.07 13.0
    12,459.49 (S)
    12,59,4
    11.96
    11.9
    13.67 13.6
    14.83 11.32 (3) 14.811.4
    5.50
    5.5
    5.96
    6.0
    13.4910.30 (8)
    13.5510.4
    13.07
    13.1
    15
    1287752
    16 Continuation of table 2
    44
    ,
    321.4
    Table continuation
    Table 4
    A sh
    4k
    vC
    in in
    ml cbli t k
    C he vO vC
    with
    AG
    0
    d
    cm
    o see
    see cm
    I
    with f
    about
    Cg
    about with
    o oh t-- oh oh
    about
    S
    )
    I r
    about jg
    about
    S
    oh oh
    &
    ЫEd
    :her
    cm
    g
    27
    60 62
    63 64
    Editor M.Kelemes Order 7732/61
    Tehred I.Popovich
    Corrector v.But
    Circulation 371 Subscription
    VNIIPI USSR State Committee for Inventions and Discoveries 113035, Moscow, Zh-35, 4/5 Raushsk nab.
    Production and printing company, Uzhgorod, st. Project, 4
    128775228
    Continued table. 6
    50 10
    50 50
    Corrector v.But ha
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    同族专利:
    公开号 | 公开日
    FI833055A|1984-02-28|
    AR241020A2|1991-04-30|
    DK390583D0|1983-08-26|
    GB2128989B|1986-03-19|
    GR79375B|1984-10-22|
    IE55900B1|1991-02-14|
    US4532243A|1985-07-30|
    AU559419B2|1987-03-12|
    IL69417D0|1983-11-30|
    AU1846183A|1984-03-01|
    PT77258B|1986-03-21|
    EP0104104B1|1986-09-24|
    AR241020A1|1991-04-30|
    CA1228589A|1987-10-27|
    US4588720A|1986-05-13|
    ES8506314A1|1985-07-01|
    ES525186A0|1985-07-01|
    DE3366467D1|1986-10-30|
    KR890003000B1|1989-08-18|
    GB2128989A|1984-05-10|
    EP0104104A1|1984-03-28|
    FI74010C|1987-12-10|
    IL69417A|1987-12-20|
    GB8322993D0|1983-09-28|
    IE832001L|1984-02-27|
    KR840005812A|1984-11-19|
    DD215550A5|1984-11-14|
    DK390583A|1984-02-28|
    NZ205387A|1986-06-11|
    PH20037A|1986-09-04|
    FI74010B|1987-08-31|
    PT77258A|1983-09-01|
    FI833055A0|1983-08-26|
    引用文献:
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    GB8334210D0|1983-12-22|1984-02-01|Roussel Lab Ltd|Imidazopyrimidines|
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    GB8613591D0|1986-06-04|1986-07-09|Roussel Lab Ltd|Chemical compounds|
    GB8620060D0|1986-08-18|1986-10-01|Roussel Lab Ltd|Chemical compounds|
    US4731446A|1987-05-01|1988-03-15|The Dow Chemical Company|Imidazo[1,2-a]pyrimidine sulfonic acids and acid halides|
    GB8712466D0|1987-05-27|1987-07-01|Roussel Lab Ltd|Chemical compounds|
    GB8719368D0|1987-08-15|1987-09-23|Wellcome Found|Heterocyclic compounds|
    US5302586A|1991-12-19|1994-04-12|G. D. Searle & Co.|Phosphonomethyl-imidazo[1,2-a]pyrimidine-2-carboxylic acid compounds for treatment of neurotoxic injury|
    CN1499972A|2001-01-26|2004-05-26|布里斯托尔-迈尔斯斯奎布公司|Imidazolyl derivatives as corticotropin releasing factor inhibitors|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB8224606|1982-08-27|
    GB838303612A|GB8303612D0|1983-02-09|1983-02-09|Imidazo 1,2-a pyrimidines|
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